Novel oxylipins from the temperate red alga Polyneura latissima: evidence for an arachidonate 9(S)-lipoxygenase

Lipids. 1997 Mar;32(3):231-5. doi: 10.1007/s11745-997-0029-9.

Abstract

The oxylipin chemistry of the temperate red alga Polyneura latissima has been investigated. The structures of three novel oxylipins, 8-[1'(Z),3'(Z),6'(Z)-dodecatriene-1'-oxy]- 5(Z),7(E)-octadienoic acid, 7(S*)-hydroxy-8(S*),9(S*)-epoxy-5(Z),11(Z),14(Z)-eicosatrienoic acid, 7(R*)-hydroxy-8(S*),9(S*)-epoxy-5(Z),11(Z),14(Z)-eicosatrienoic acid, together with two known eicosanoids, 9(S)-hydroxy-5(Z),7(E),11(Z),14(Z)-eicosatetraenoic acid, and 9,15-dihydroxy-5(Z),7(E),11(Z),13(E)-eicosatetraenoic acid, were elucidated by spectroscopic methods and chemical degradation. The oxygenation pattern of these oxylipins suggests that P. latissima metabolizes polyunsaturated fatty acids via a 9(S)-lipoxygenase.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Arachidonate Lipoxygenases / metabolism*
  • Arachidonic Acids / chemistry*
  • Eicosanoids / chemistry*
  • Eicosanoids / metabolism
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Rhodophyta / chemistry*
  • Rhodophyta / metabolism
  • Spectrum Analysis

Substances

  • Arachidonic Acids
  • Eicosanoids
  • Arachidonate Lipoxygenases